How To Wear an Oversized Shirt

Women's oversized shirts first became popular in the 1990s. Back then, it was trendy among the urban youth. Young people wore oversized t-shirts with baggy jeans and sneakers to look cool.

Now, though, the oversized shirt has evolved significantly. It's not just something that you see people wearing down dark alleyways and beside city basketball courts. It's a bona fide fashion statement.

With that said, there is something of an art to wearing an oversized tee. Just wearing oversized clothing without thinking about how you're putting the whole outfit together will land you in trouble.

Fortunately, this post is here to help. In it, we explain how to wear oversized shirts and look great at the same time. But first, what exactly is an oversized t-shirt?

What is an oversized t-shirt?

Technically speaking, any t-shirt that is too large for you is oversized. But when fashionistas say "oversized shirt," they mean something quite specific: a tee that is deliberately loose fit and hangs down well below the waist.

On catwalks, oversized button-down shirts are common. These are ideal for anyone looking to create a casual outfit. You don't have to follow in their footsteps, though. An oversized graphic tee or white cotton shirt can both look great as well.

How big should oversized shirts be?

Generally, you'll want to go around two sizes larger than your regular size when choosing an oversized shirt. It should be loose fitting over the shoulders and conceal part of the hand (if long-sleeved).

The type of oversized shirt you wear will depend on the occasion. If you are planning on wearing it out of the house, then the best oversized shirts are plain. These have a semi-formal appearance and tend to work well when worn with other fashionable items. The same goes for a traditional white oversized shirt. These, too, look great out and about, particularly in the summer months.

Of course, if you're looking for something to lounge about the house in, then you'll want something a little less formal. A regular oversized graphic tee will do.

Oversized shirt outfit ideas

So, without any further ado, let's take a look at some of the ways you can style oversized shirts.

Go for the athleisure look

If you want to wear an oversized shirt for doing exercise at home, you have plenty of options. The most popular combination is to pair an oversized top with tight leggings. This gives you freedom of movement while also helping you feel relaxed.

Create a mini skirt

Another idea is to turn your oversized shirt into a mini skirt. You can do this by wearing a leather jacket over it. The jacket should cinch the waist, allowing the rest of the t-shirt to flow elegantly below. Wear bear legged or with tights and round off the look with heels for maximum effect.

Wear with skinny jeans

Another great idea is to combine your oversized shirt outfits with skinny jeans. Thin denim legs, strappy sandals, and a baggy button-down shirt or sweater work well together.

If you want to make the outfit a little edgier, pair it with white sneakers and add a cinch around the waist. 

Go all-white

Another option is to go all-white, as shown here. Pure white is a great option for anyone with darker skin as it creates a beautiful contrast. Adding black or pale blue jeans (regular wardrobe staples) is all you need to complete the look.

Go back to your skater days

If you miss your skater days and want to go back and celebrate them, this outfit concept should be right up your street. Try pairing an oversized tee with a long sleeve sheer inner, light jeans, and jewelry for a relaxed look. It's the perfect outfit for looking great while running errands at the same time.

Striped pants

Oversized tees also pair well with striped pants, as you can see here. Pairing black and copper works well and helps to give the outfit a finished, polished, look. Images of skeletons popping wheelies adds to the fun factor. 

Knot it around the waist

If you're not a big fan of baggy clothes but still want to jump on the bandwagon, you can style an oversized shirt by knotting it around your waist. This way, you can make a classic shirt look fitted.

To do this, take the bottom of the shirt and then roll the material up to waist height, then tie it in a simple bow at the front. (You should have plenty of extra fabric if the shirt is large enough). Then simply pair with blue jeans or, better yet, Korean-style pants, a handbag, and sandals. 

Go for the half-tuck

Letting oversized shirts drape below the waist fully can look good. But if you want to add a little asymmetry to your style, you might want to go for the half-tuck. Then pair with a denim jacket, eye wear, and heels for date night.

Tuck it in completely

Alternatively, you're free to tuck your shirt into your pants completely, letting it hang out slightly around the waistline, giving you a mushroom-like silhouette. Try this style with traditional French or Italian pumps, blue jeans, and a white belt around the middle to give you more shape. 

Pair it with heels

High heels and bare legs complement a chic baggy top perfectly. The extra height adds length to your silhouette, helping to make the entire outfit more balanced, while the bare legs make the ensemble perfect for the summer heat. It's the ideal setup for BBQs, days out on the town, or even shopping trips. 

Go sleeveless

If you want to show off your arms and stay cool at the same time, going sleeveless is a great idea. Plus, if you get it right, it looks quite formal, too.

Pick any sleeveless plain oversized shirt and make sure that it hangs down below your waist. Then pair with three-quarter-length pants, and an optional belt around the middle. Add classic, behind-the-ankle platform sandals and clutch to complete the look.

Turn it into a dress

You can turn any type of oversized shirt into a dress. But button-down varieties are arguably the most dramatic. When worn loose enough, they go as low as the knees, flaring out at the sides.

Set yourself up for the perfect beach day

Styling ideas for the beach can be quite limited. But when you think about it, oversized tees are perfect for this. They're casual, warm, and great for covering you up (if needed) while enjoying the coast.

We recommend wearing a yellow or blue shirt with denim shorts over your bathing suit for an edgy, summer look.

Master your lounge suit

Oversized shirts are also the perfect complement to your lounge suit. We like this concept because it adds a little fun and unashamed joy to the mix. After all, when you're in full-blown hygge mode, you want to feel great.

In this example, we have a smiley-faced oversized sweater paired with work shoes and faux leather black pants. However, this setup will work just as well with pajama bottoms and slippers.

Wear power boots

Mixing the relaxed aesthetic of oversized shirts with power boots creates a dramatic look that instantly makes you stand out. The bulkiness of the top and boots offset the skinniness of the thighs in the middle for a more balanced appearance.

Try lavender

Lavender is the perfect color for a lazy day. Not only does it look great on any pull, but the herb is also famous for boosting peace of mind.

You can either wear an oversized lavender shirt loose or with a French tuck.

Celebrate your love of sports

While very different from a crop top, there is something fundamentally sporty about wearing an oversized shirt, probably because of the association with basketball players.

Here's an idea: wear a large black tee with sporting emblems on the front paired with tight white pants. The combination is casual enough for wearing in the house, but also smart enough for errands to the store. This example works well for anyone who loves tennis.

Go for a tank-style look

You could also try a tank top-style look. This setup is perfect for spending time outdoors on sunny days or keeping yourself cool during high heat. The open arms, neck, and shoulders keep trapped perspiration to a minimum.

If things get a little cold, pair the top with a waist jacket to create a slip-dress effect at the bottom. Finally, add Italian pumps as footwear.

Wrapping Up

As you can see from these styling tips, there are innumerable ways to wear oversized shirts. The world is very much your oyster.

The key takeaway here is not to be afraid of experimentation. If you want to try something, go for it. Use these examples of templates.